No.10 – Definitely, Maybe (2008)

In a rom-com that somewhat mimics CBS’ How I Met Your Mother, Ryan Reynolds plays a father who tells his ten-year-old daughter (Abigail Breslin) the stories of his previous romantic escapades, including how he ended up marrying her mother, to help explain his impending divorce. Isla Fisher, Rachel Weisz, and Elizabeth Banks are all featured in this charming and perceptive romantic dramedy.

No.9 – Adventureland (2009)

The comedy Adventureland, written and directed by Greg Mottola of Superbad, is based in part on the upstate New York theme park and centers on summertime park employees in 1987. Reynolds has a supporting role as the senior maintenance worker for the Fun Zone, but it’s still a great opportunity to employ him in the ensemble (while also paying homage to his previous “big fish in a little pond” performances he’d had in Waiting and Van Wilder). Jesse Eisenberg and Kristen Stewart play the leading characters, in addition to Reynolds, Kristen Wiig, Bill Hader, and Martin Starr.

No.8 – The Proposal (2009)

The Proposal, a 2009 release from Step Up and 27 Dresses actress Anne Fletcher, was like a charismatic eruption. Reynolds and Sandra Bullock starred in this romantic comedy, in which a female executive persuades her assistant to act as her fiancé in order to avoid being deported to Canada. Since they both possessed impeccable comedic timing and the ability to bounce off one another, Reynolds and Bullocks exhibited fantastic chemistry in this scene. Additionally included are Malin Akerman, Craig T. Nelson, Mary Steenburgen, and Betty White.

No.7 – Buried (2010)

tension-filled thriller Buried, a 2010 film, was Reynolds’ next daring step. However, it was effective in relieving a lot of tension with very little effort. He was taken captive in Iraq while working as an American truck driver, and before being buried alive in a coffin, he was only given a lighter, flask, flashlight, knife, glow sticks, pen, and cell phone. Reynolds portrayed a guy battling for his life in this moment’s crucible in a frantic, dramatic performance.

No.6 – Deadpool 2 (2018)

No.5 – Free Guy (2021)

Free Guy, which released after numerous disastrous delays to a healthy box office take, starred Ryan Reynolds as an NPC in a GTA-style MMO who gains sentience and falls in love with a real-life player character. Reynolds proved through the success of Free Guy that he could develop a unique character with a memorable concept and endearing, self-aware humor. Jodie Comer, Lil Rel Howery, Utkarsh Ambudkar, Joe Keery, and others co-star with Taika Waititi in the film.

No.4 – Pokemon Detective Pikachu (2019)

Ryan Reynolds lent his warm whimsy to Detective Pikachu in the upcoming action-mystery Pokemon film Detective Pikachu. Ryan Reynolds’ charm (and facial-motion capture) as the coffee-obsessed investigator in Detective Pikachu, which also starred Justice Smith, Kathryn Newton, Ken Watanabe, and Bill Nighy, made it a special delight among video game movies. Reynolds’ portrayal was endearingly comic and more in tune with his subversive Deadpool persona than you might expect from a Pokemon movie.

No.3 – The Adam Project (2022)

Shawn Levy, the director of Stranger Things and Free Guy, scored a stylish, futuristic family adventure with Netflix’s The Adam Project that wonderfully captured the spirit of ’80s sci-fi. Reynolds plays a pilot from a bleak future who travels back in time to learn what happened to his wife, but who ends up in the incorrect year and runs across his younger, 12-year-old self (Walker Scobell). The Adam Project is a witty parody of films like Back to the Future, The Last Starfighter, and others, and it also stars Mark Ruffalo, Jennifer Garner, and Zoe Saldaa. Our ranking of the best science fiction movies on Netflix includes more movies like this.

No.2 – Mississippi Grind (2015)

One of the less well-known films on this list, Mississippi Grind, stars Reynolds and Ben Mendelsohn and was directed by the (final) Captain Marvel directors Anna Boden and Ryan Fleck. It’s a drama about a gambler who thinks his new companion (Reynolds) is a lucky charm and is traveling to a high-stakes poker game in New Orleans. Together, Reynolds and Mendelsohn create a tragicomic character study that endures forever.

No.1 – Deadpool (2016)

Finally, Ryan Reynolds has found the role for which he was created. Reynolds first appeared in 2009’s X-Men Origins: Wolverine as the mercenary Wade Wilson, and the hiring of Reynolds as Deadpool was dreadfully teased at the time (who was robbed of his ability to speak and snark in the third act). Deadpool, directed by Tim Miller, got everything right, though, and it was an instant success. Deadpool was a comedy-action triumph with hilarious one-liners, great action, and a ton of fun fan service.

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